CRO Calendly, Kate Ahlering: Embracing Leadership - On and Off the Basketball Court
Grit21 Feb 2022

CRO Calendly, Kate Ahlering: Embracing Leadership - On and Off the Basketball Court

Kate Ahlering might be the perfect guest for this podcast. She eventually worked her way up to Chief Sales Officer of Glassdoor, but when she joined in 2013, she helped define the company’s leadership framework as GRIT: Growth, Results, Integrity, and Team. Glassdoor has continued using those values since her departure in 2020, and now as the CRO of Calendly, she is applying a similar framework to another fast-growing enterprise.


In this episode, Kate and Joubin discuss her first leadership experience, captaining her college basketball team before ever playing a game; the wild ride of working at Glassdoor when it was doubling every year; the perspective and confidence that comes from working experience; brokering consensus when deciding a company’s values; the increasingly complex use cases for Calendly; and a ridiculous Twitter feud over “Calendly etiquette.”


In this episode, we cover:

  • Kate and Joubin’s past interactions, including a disagreement over San Diego cuisine (03:02)
  • How being raised by two salespeople and playing basketball at the University of Virginia shaped Kate’s worldview (06:01)
  • Working at Glassdoor “never felt easy,” but she later realized it was a once-in-a-lifetime experience (14:47)
  • Her big legacy at Glassdoor, defining its values as GRIT: Growth, Results, Integrity, and Team (20:38)
  • Building trust with a team in a rapidly-changing environment, and working alongside Indeed — a former competitor now owned by Glassdoor’s parent company (26:16)
  • Calendly’s interview process and the dangers of offering a thorough plan before you’re inside the company (32:08)
  • The surprising depths of Calendly’s complexity in enterprise, and why founder Tope Awotona (accidentally) made the business model freemium (36:15)
  • Kate could have gone almost anywhere after Glassdoor — why she chose Calendly, and what motivated her to achieve? (42:36)
  • When she’s going to bed every night, what does Kate wish she was spending more time on? (48:14)



Links:

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Chief Sales and Success Officer at Slack, Bob Frati: Exploring Slack’s Key Growth Levers and Competition

Chief Sales and Success Officer at Slack, Bob Frati: Exploring Slack’s Key Growth Levers and Competition

In Episode #1 of Go to Market Grit, Slack’s SVP of Sales and Customer Success, Bob Frati, gives the inside scoop about the company’s sales and go-to-market strategy, and why they have been able to scale their go to market so quickly and effectively over the last few years. Bob and Joubin discuss two key topics in detail, outlining the next four years for Slack and key growth levers they can pull, along with growing competition in Slack’s market and what that means for their future. In this episode of Go to Market Grit, we cover: Key growth levers for Slack, and why the company is positioned for continued market dominance.Slack’s response to growing market competition, and why it’s ultimately better for the consumer and for the company.How Slack identified a business need and strong product market fit, and then worked to expand the solution to a broader audience. The importance of having a strong and developed customer-facing team to navigate complexities in large enterprises, and push business forward to completion.How Slack grew its sales team from 300 to 2,000 people — quickly, and effectively. Some of the factors that Slack looks for when hiring customer-facing sales staff, and why they value these characteristics.Why hiring should be a mutual fit for both the candidate and the employer.Identifying motivated individuals, and finding ways to tap into their motivation that will drive them to be successful. Bob’s career journey from sales rep to manager — including why and how he executed the leap. Why much of Slack’s success can be attributed to tight collaboration between its engineering, product, sales, and success teams. Slack’s ability to not only deploy a solution in an organization, but to help manage through the change and ensure success — and why this is a game-changer.Slack’s role in ushering a new way of working, and why it transcends the tired and overused digital transformation narrative in business.Links Host company: https://www.kleinerperkins.com/Loom: https://www.loom.com/ Guest LinkedIn: https://www.linkedin.com/in/rfrati/Host Twitter: https://twitter.com/JoubinmirHost Email: gtmg@kleinerperkins.com

16 Juni 202050min

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Grit Trailer

About the Joubin MirzadeganJoubin has been with Kleiner Perkins since 2019 where he advises the KP portfolio companies on how to build and scale a robust go-to-market strategy. Additionally, he enables the firm’s portfolio through high impact relationships with F500 executives and key ecosystem partners. Joubin was previously at Palo Alto Networks as a global district sales manager for the Central US based in Chicago where he scaled the Central Cloud business from 1 enterprise rep and $2M ARR to 12 reps and $50M+ ARR in 4 quarters. He has also worked for Evident.io as an enterprise account executive and at Bracket Computing (acquired by VMWare) where he built the inside sales team from the ground up.

20 Apr 202045s

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